It’s a Tuesday night at LIV nightclub on U Street NW, and Mambo Sauce vocalist Black Boo has broken into a reggae-tinged Waka Flocka Flame mash-up. The crowd is feeling it, but standing on stage, Demont “Peekaso” Pinder is facing the other way.

In one hand he holds an iPad, displaying the worn face of Miles Davis, anxious in black and white. In the other hand, Peekaso has a paintbrush, and over a background of reds, whites, and greens he aggressively translates the visage of the iconic trumpeter.

Peekaso’s appearance is basic enough: a white T-shirt, a yellow knit skull cap that rests lazily on the crown of his head, a yellow rag dangling from the back right pocket of his blue jeans. As Black Boo and the crowd feed off each other, chaos seems to close in on the painter, who doesn’t sweat it. He cracks a joke and finishes his Miles opus.

Five days later, the mood is euphoric at U Street Music Hall. Producers Kev Brown, Bink!, 88 Keys, and DJ Spinna are selecting gems from their catalogs, and Peekaso is silent, coolly nodding his head as he takes in the scene. On the canvas, he paints four silhouettes at a soundboard against a florescent backdrop.

The next Saturday, Chuck Brown is at the 9:30 Club, pounding through his vast go-go repertoire with his vast go-go band. The lights flicker, fans sway, and performers gyrate as Peekaso paints a big-faced portrait of the famous bandleader.

“I’m everywhere,” says Peekaso, a 31-year-old single father who lives in Laurel. “I’ve gotta make it happen and I can’t take no for an answer.”

Since 2003, Peekaso has been the art director of local crooner Raheem DeVaughn, the city’s biggest R&B export, creating art for his albums and as a member of the singer’s touring band—only, Peekaso doesn’t play an instrument. During concerts, he simply paints.

In recent years, Peekaso has become a mainstay if also an outlier on the city’s hip-hop, go-go, and R&B circuits. His raw images are equal parts jazz-age portraiture and graffiti-tinged neo-expressionism, and on stage, he paints like rappers spit—furiously, but with precision. At a 9:30 Club benefit concert for Haitian earthquake relief in January, Peekaso created an arresting scene of devastation while DeVaughn performed with rappers like Wale and Tabi Bonney. Toward the end of the night, the painting was auctioned off for $600.

Two years ago, Peekaso painted a picture for Bonney to commemorate “The Pocket,” the D.C. rapper’s regional radio hit from 2006. That portrait, complete with the U.S. Capitol and the dreadlocks Bonney once wore, hangs on the wall of Bonney’s parents’ living room.

“He’s a bad man, for certain,” says LaVar Arrington, the former Redskins linebacker, who has four Peekaso pieces. “I hope he has an opportunity to get his name out there more. He’s one of those types of guys that people should be paying attention to, so he can become a household name someday.”

Peekaso’s work dots restaurants along U Street NW, and he often gives his work to local notables to increase his profile. These days, most of his income goes to supporting his 8-year-old daughter. To make ends meet, Peekaso often raffles off or auctions his paintings at open-mic events and concerts. At the regular Up and Up open mics at LIV, for instance, he usually paints two pieces: one that can be purchased outright and another that’s won through a $1 lottery.

Peekaso has also found commissions through his DeVaughn connection: WKYS-FM host Russ Parr, for instance, asked Peekaso to paint a mural in his home. “It just comes when it comes,” Peekaso said. “I get it how I can get it.”

As a portraitist, Peekaso seems to focus chiefly on celebrities, local and otherwise—mostly prominent African-Americans in culture and politics. The pictures can be reverent or playful or otherworldly—and frequently funny. Take his painting of Kanye West and Taylor Swift at the 2009 MTV Video Music Awards; a cloudy thought bubble emerges from the latter’s head, screaming “WTF?”

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Peekaso was born in Queens, N.Y., and his story is dotted with school transfers, evictions, and professional uncertainty—experiences he says he channels in his work. In the late 1980s, his mother moved with him from Queens to Maryland, looking for more space and better opportunities. He attended elementary schools in Bladensburg and Landover Hills. As a seventh-grader at Robert Goddard Middle School in Seabrook, he designed the school’s yearbook cover, although his copy was lost during one of his family’s evictions.

Peekaso’s life settled down by the time he entered High Point High School in Beltsville. There he forged his friendship with DeVaughn, who worked at a local grocery store at the time. The two began playing pick-up basketball with each other, sometimes “bumping heads,” as Peekaso puts it.

After graduating from high school, Peekaso worked for FedEx for five years, keeping in contact with the burgeoning soul singer. As DeVaughn’s career began to take off, he asked Peekaso to travel with him and paint live on stage. “I always wanted to have an artist on stage with me,” DeVaughn says. “I asked him, ‘How much do you make a week? You could make that, if not more, by painting.’”

Both DeVaughn and Peekaso admit that touring has strained their friendship, at least somewhat. The two are not as personable on tour, Peekaso says, and sometimes he gets the most criticism. “At the end of the day, that’s my boss, but he’s still my brother,” Peekaso says.

“I’m tough to work for at times,” DeVaughn says. “In the end, he’s got a job to do. He’s definitely an asset to what I’ve built. It’s a win-win for both of us.” Peekaso is paid per gig as a member of DeVaughn’s band, sometimes getting a weekly salary if the vocalist goes on tour. This summer, DeVaughn embarked on a 20-city trek to promote his album The Love & War Masterpeace.

But Peekaso has bigger dreams. He wants to buy his mother a house, and open art galleries in D.C., Los Angeles, and Miami to display his paintings. On Jan. 10, he’ll travel to New York for a demonstration at the Apple store in SoHo; recently he’s begun creating intricate works on his iPad.

One prominent local collection where you can’t see Peekaso’s work yet is the D.C. government’s. But Zoma Wallace, who manages the art in city buildings, says she’s been a fan of Peekaso’s work since it appeared on DeVaughn’s 2005 debut album, The Love Experience. She says Peekaso’s work would be “an incredible addition” to the city’s collection, which grows each summer when the D.C. Commission on the Arts and Humanities put out a call to working artists. “The speed in which he executes his work is also quite impressive,” Wallace says. “You don’t see him on stage with anything but his materials and easel, so he literally creates his art on the move. There is no smoke and no mirror in his process.”

D.C. Councilmember Yvette Alexander only paid $50 at an auction for her Peekaso picture of Marvin Gaye, although she says she would’ve spent more. Peekaso’s usual asking price starts at $400. But the Ward 7 councilmember thinks Peekaso’s association with the city’s music scene may have also limited his reach. “He needs to feel out where people will appreciate his work,” she says. “He’s in the wrong demographic right now for what he does. He should’ve upped his price a long time ago.”